Triacetin

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Triacetin[1]
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Names
Systematic IUPAC name
Propane-1,2,3-triyl triacetate
Other names
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  • Glycerol triacetate
  • glycerin triacetate
  • 1,2,3-triacetylglycerol
  • 1,2,3-triacetoxypropane
Identifiers
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3D model (JSmol)
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  • InChI=1S/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3 checkY
    Key: URAYPUMNDPQOKB-UHFFFAOYSA-N checkY
  • InChI=1/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3
    Key: URAYPUMNDPQOKB-UHFFFAOYAH
  • CC(=O)OC(COC(=O)C)COC(C)=O
Properties
C9H14O6
Molar mass 218.205 g·mol−1
Appearance Oily liquid
Density 1.155 g/cm3[2]
Melting point −78 °C (−108 °F; 195 K)[4]Template:Rp
Boiling point 259 °C (498 °F; 532 K)[4]Template:Rp
6.1 g/100 mL[3][page needed]
Solubility in ethanol Miscible
Solubility in benzene soluble
Solubility in diethyl ether soluble
Solubility in acetone very soluble
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  • 1 Pa (0.0075 mmHg) (37.6 °C (99.7 °F; 310.8 K))
  • 10 Pa (0.075 mmHg) (62 °C (144 °F; 335 K))
  • 100 Pa (0.75 mmHg) (90 °C (194 °F; 363 K))
  • 1 kPa (7.5 mmHg) (124 °C (255 °F; 397 K))
  • 10 kPa (75 mmHg) (165 °C (329 °F; 438 K))
  • 100 kPa (750 mmHg) (214 °C (417 °F; 487 K))[4]Template:Rp
1.4301 (20 °C (68 °F; 293 K))[4]Template:Rp
Viscosity 23 mPas (20 °C (68 °F; 293 K))[2]
Thermochemistry[5][4]Template:Rp
389 J⋅mol−1·K-1
458.3 kJ⋅mol−1·K-1
−1330.8 kJ⋅mol−1
4211.6 kJ⋅mol−1
Hazards[2]
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0
1
0
Flash point 138 °C (280 °F; 411 K)
430 °C (806 °F; 703 K)
Explosive limits 7.73%-?
Lethal dose or concentration (LD, LC):
3 g/kg (rat, oral)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Triacetin is the organic compound with the formula Page Module:Chem2/styles.css has no content.C3H5(OCOCH3)3. It is classified as a triglyceride, i.e., the triester of glycerol with acetic acid. It is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations.[6] It is one of the glycerine acetate compounds.

Uses

Triacetin is a common food additive, for instance as a solvent in flavorings, and for its humectant function, with E number E1518 and Australian approval code A1518. It is used as an excipient in pharmaceutical products, where it is used as a humectant, a plasticizer, and as a solvent.[7]

Potential uses

The plasticizing capabilities of triacetin have been utilized in the synthesis of a biodegradable phospholipid gel system for the dissemination of the cancer drug paclitaxel (PTX).[8] In the study, triacetin was combined with PTX, ethanol, a phospholipid and a medium chain triglyceride to form a gel-drug complex. This complex was then injected directly into the cancer cells of glioma-bearing mice. The gel slowly degraded and facilitated sustained release of PTX into the targeted glioma cells.

Triacetin can also be used as a fuel additive as an antiknock agent for gasoline, and to improve low-temperature viscosity properties of biodiesel.[9]

It has been considered as a possible source of food energy in artificial food regeneration systems on long space missions. It is believed to be safe to get over half of one's dietary energy from triacetin.[10]

Synthesis

Triacetin was first prepared in 1854 by the French chemist Marcellin Berthelot. Triacetin was prepared in the 19th century from glycerol and acetic acid.[11][12]

Its synthesis from acetic anhydride and glycerol is simple and inexpensive:

Page Module:Chem2/styles.css has no content.3 (CH3CO)2O + C3H5(OH)3 → C3H5(OCOCH3)3 + 3 CH3CO2H

This synthesis has been conducted with catalytic sodium hydroxide and microwave irradiation to give a 99% yield of triacetin.[13] Synthesis has also been conducted with a cobalt(II) Salen complex catalyst supported by silicon dioxide and heated to 50 °C (122 °F) for 55 minutes to give a 99% yield of triacetin.[14]

Safety

The US Food and Drug Administration has approved it as generally recognized as safe food additive and included it in the database according to the opinion from the Select Committee On GRAS Substances (SCOGS). Triacetin is included in the SCOGS database since 1975.[15][16]

Triacetin was not toxic to animals in studies of exposure through repeated inhalation over a relatively short period.[17]

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. p. 9405. ISBN 091191028X.
  2. ^ a b c d Page Module:Citation/CS1/styles.css has no content."Triacetin SDS". fishersci.com. ThermoFisher Scientific. Retrieved 2025-12-05.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Lide DR, ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  4. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.Lide D, ed. (2004). CRC Handbook of Chemistry and Physics (85th ed.). Boca Raton, Florida: CRC Press. ISBN 978-0-8493-0485-9.
  5. ^ Template:Nist
  6. ^ Page Module:Citation/CS1/styles.css has no content.Arctander S (1969). Perfume and Flavor Chemicals (II K - Z). Elizabeth, N.J.: Published by the Author. p. 2971. ISBN 978-0-931710-37-7.
  7. ^ Page Module:Citation/CS1/styles.css has no content."Triacetin". drugtopics.modernmedicine.com. Advanstar Communications, Inc. Archived from the original on 2012-02-19. Retrieved 2014-06-20.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Chen T, Gong T, Zhao T, Liu X, Fu Y, Zhang Z, et al. (August 2017). "Paclitaxel loaded phospholipid-based gel as a drug delivery system for local treatment of glioma". International Journal of Pharmaceutics. 528 (1–2): 127–132. doi:10.1016/j.ijpharm.2017.06.013. PMID 28596136.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Gupta M, Kumar N (2012). "Scope and opportunities of using glycerol as an energy source". Renewable & Sustainable Energy Reviews. 16 (7): 4551–4556. Bibcode:2012RSERv..16.4551G. doi:10.1016/j.rser.2012.04.001.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Shapira J, Mandel AD, Quattrone PD, Bell NL (1968). "Current Research On Regenerative Systems" (PDF). Life Sciences in Space Research. 7. Tokyo: Committee On Space Research, Eleventh Annual Meeting: 123–9. PMID 12197534. Retrieved 2024-07-16.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Berthelot M (1854). "Sur les combinaisons de le glycérine avec les acides et sur la synthèse des principes immédiats des graisses des animaux" [On the compounds of glycerin with acids and on the synthesis of immediate principles of animal fats]. Annales de Chimie et de Physique. 3rd series (in French). 41: 216–319.{{cite journal}}: CS1 maint: unrecognized language (link)
  12. ^ Page Module:Citation/CS1/styles.css has no content."Preparation of glyceryl triacetate". Journal of the Chemical Society, Abstracts. 38: 312. 1880. doi:10.1039/CA8803800307.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Rajabi F, Saidi MR (2005). "A Cheap, Simple, and Versatile Method for Acetylation of Alcohols and Phenols and Selective Deprotection of Aromatic Acetates Under Solvent-Free Condition". Synthetic Communications. 35 (3): 483–491. doi:10.1081/SCC-200048988. ISSN 0039-7911. S2CID 96001761.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Rajabi F (2009). "A heterogeneous cobalt(II) Salen complex as an efficient and reusable catalyst for acetylation of alcohols and phenols". Tetrahedron Letters. 50 (4): 395–397. doi:10.1016/j.tetlet.2008.11.024.
  15. ^ Page Module:Citation/CS1/styles.css has no content."21 CFR § 184.1901 Listing of Specific Substances Affirmed as GRAS: Triacetin". eCFR.gov. FDA. 21 Feb 1989. Retrieved 25 Apr 2023.
  16. ^ Page Module:Citation/CS1/styles.css has no content."Glycerin and Glycerides". www.fda.gov. U.S. Food and Drug Administration. Archived from the original on 2017-10-31. Retrieved 2014-06-20. Triacetin and two types of acetooleins have been found to be without toxic effects in long-term feeding tests in rats at levels that were several orders of magnitude greater than those to which consumers are exposed.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Fiume MZ (2003). "Final report on the safety assessment of triacetin". International Journal of Toxicology. 22 Suppl 2 (3): 1–10. doi:10.1080/747398359. PMID 14555416.

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